We are utilizing the conversion of lactams to cyclic enamines in the synthesis of vobasine-sarpagine and eburine-vincadifformine alkaloids. These alkaloids represent one-half of several of the Vinca rosea dimeric indole alkaloids, such as vinblastine, vincristine, and voacamine, the first two of which are powerful anti-tumor agents. The partial reduction of lactams to enamines uses a metal hydride and a trapping agent (secondary amine or cyanide) to prevent further reduction of the enamine. The use of sodium borohydride in neat carboxylic acid media will be explored as a new method for accomplishing ionic hydrogenation and amine reductive-alkylation.